Nitric Acid → Methyl 5-methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 1862044Notes

Reaction equation

HRID 1862044 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:8]2.[N+:17]([O-])([OH:19])=[O:18].C(OCC)C>C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:17]([O-:19])=[O:18])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:8]2

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 13058285Methyl 5-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Product 1

HCID 18622485Methyl 5-methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylateYield 20%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Methyl 5-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate (1.1 g, 5 mmol; described in: Johnson, D. W.; Mander, L. N. Aust. J. Chem. 1974, 8, 1277-1286) dissolved in acetic anhydride (20 mL), was treated with 70% nitric acid (0.4 mL) at 0 C for 1 h and the mixture was poured into ice-water and diethyl ether. The organic phase was separated, evaporated in vacuo and the residue triturated with diisopropyl ether to yield 0.27 g (20%) of the title compound as crystals: mp 100-104° C.; EIMS (20 eV) m/z (relative intensity) 265 (35, M+).

Workup

  1. customThe organic phase was separated
  2. customevaporated in vacuo
  3. customthe residue triturated with diisopropyl ether

Sources & evidence

ORD record
ord-34994dfe0e6d47c1861603db53c8828a
Source dataset
uspto-grants-2003_03
Patent number
US06534652B2

Reaction notes

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